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Phenol → Methyl 2-(4-methyl-6-phenoxy-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399644
ノート
印刷プレビュー

反応式

HRID 1399644 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:15]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:19]([CH3:29])[N:18]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:29][C:19]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:16]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

生成物 1

HCID 66955927Methyl 2-(4-methyl-6-phenoxy-2-phenylpyrimidin-5-yl)pentanoate収率 68.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 516892
Sodium Bicarbonate
溶媒

反応条件

温度
100 °C

実験手順

Phenol (0.141 g; 1.5 mmol) and cesium carbonate (0.489 g; 1.5 mmol) were added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL) and heated in a seal tube to 100° C. for 18 h. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.129 g (58%) of the title compound.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane

出典と根拠

ORDレコード
ord-4b930a33b41844bf9f4c291cf586b28c
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08906906B2

反応ノート

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